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Cheap flights from Illinois to Anguilla from $425

This is the cheapest one-way flight price found by a momondo user in the last 72 hours by searching for a flight from Illinois to Anguilla departing on 2/4. Fares may change, and may not be available for all flights or travel dates. Click the price to refresh the search for this deal.
1 adult
1 adult, Economy, 0 bags

Discover deals from 900+ travel sites with momondo.

Find the cheapest flights from Illinois to Anguilla

Cheap round-trip flights

Enter your travel dates to find the best prices.
American Airlines Logo
7:50 pm - 2:57 pmORD  Chicago O'Hare Intl-AXA The Valley Wallblake Intl
17h 07m1 stop Miami
American Airlines Logo
3:37 pm - 12:44 amAXA  The Valley Wallblake Intl-ORD Chicago O'Hare Intl
11h 07m1 stop Miami
$712American Airlines
Tue, Dec 8 - Tue, Dec 15
American Airlines Logo
9:06 pm - 2:57 pmORD  Chicago O'Hare Intl-AXA The Valley Wallblake Intl
15h 51m2 stops Charlotte Douglas Miami
American Airlines Logo
5:45 pm - 7:27 amAXA  The Valley Wallblake Intl-ORD Chicago O'Hare Intl
15h 42m2 stops Miami Philadelphia
$717American Airlines
Tue, Dec 8 - Tue, Dec 15
American Airlines Logo
9:06 pm - 2:57 pmORD  Chicago O'Hare Intl-AXA The Valley Wallblake Intl
15h 51m2 stops Charlotte Douglas Miami
American Airlines Logo
3:37 pm - 8:00 amAXA  The Valley Wallblake Intl-ORD Chicago O'Hare Intl
18h 23m1 stop Miami
$717American Airlines
Tue, Dec 8 - Tue, Dec 15
American Airlines Logo
9:06 pm - 2:57 pmORD  Chicago O'Hare Intl-AXA The Valley Wallblake Intl
15h 51m2 stops Charlotte Douglas Miami
American Airlines Logo
5:45 pm - 9:30 amAXA  The Valley Wallblake Intl-ORD Chicago O'Hare Intl
17h 45m1 stop Miami
$717American Airlines
Tue, Dec 8 - Tue, Dec 15
Multiple Airlines Logo
10:05 am - 5:25 pmORD  Chicago O'Hare Intl-AXA The Valley Wallblake Intl
29h 20m2 stops Toronto Pearson Intl Simpson Bay Princess Juliana
Multiple Airlines Logo
9:00 am - 7:55 pmAXA  The Valley Wallblake Intl-ORD Chicago O'Hare Intl
12h 55m1 stop Toronto Pearson Intl
$1,537Multiple Airlines
Sun, Dec 27 - Sat, Jan 2
Multiple Airlines Logo
3:45 pm - 5:25 pmORD  Chicago O'Hare Intl-AXA The Valley Wallblake Intl
23h 40m3 stops Montreal Pierre Elliott Trudeau Intl Toronto Pearson Intl Simpson Bay Princess Juliana
Multiple Airlines Logo
9:00 am - 7:55 pmAXA  The Valley Wallblake Intl-ORD Chicago O'Hare Intl
12h 55m1 stop Toronto Pearson Intl
$1,627Multiple Airlines
Sun, Dec 27 - Sat, Jan 2
Multiple Airlines Logo
8:55 am - 5:35 pmORD  Chicago O'Hare Intl-AXA The Valley Wallblake Intl
31h 40m2 stops San Juan Luis Munoz Marin Intl Saint Thomas Island Cyril E King
Multiple Airlines Logo
9:46 am - 8:05 pmAXA  The Valley Wallblake Intl-ORD Chicago O'Hare Intl
35h 19m2 stops Saint Thomas Island Cyril E King San Juan Luis Munoz Marin Intl
$1,634Multiple Airlines
Mon, Aug 31 - Fri, Sep 4
Multiple Airlines Logo
8:55 am - 5:35 pmORD  Chicago O'Hare Intl-AXA The Valley Wallblake Intl
31h 40m2 stops San Juan Luis Munoz Marin Intl Saint Thomas Island Cyril E King
Multiple Airlines Logo
9:46 am - 8:05 pmAXA  The Valley Wallblake Intl-ORD Chicago O'Hare Intl
11h 19m2 stops Saint Thomas Island Cyril E King Houston George Bush Intcntl
$1,634Multiple Airlines
Wed, Sep 30 - Sat, Oct 3
Multiple Airlines Logo
8:55 am - 5:35 pmORD  Chicago O'Hare Intl-AXA The Valley Wallblake Intl
31h 40m2 stops San Juan Luis Munoz Marin Intl Saint Thomas Island Cyril E King
Multiple Airlines Logo
9:46 am - 8:05 pmAXA  The Valley Wallblake Intl-ORD Chicago O'Hare Intl
35h 19m2 stops Saint Thomas Island Cyril E King San Juan Luis Munoz Marin Intl
$1,634Multiple Airlines
Mon, Aug 31 - Fri, Sep 4
Multiple Airlines Logo
3:45 pm - 5:25 pmORD  Chicago O'Hare Intl-AXA The Valley Wallblake Intl
23h 40m3 stops Montreal Pierre Elliott Trudeau Intl Toronto Pearson Intl Simpson Bay Princess Juliana
Multiple Airlines Logo
9:00 am - 8:03 amAXA  The Valley Wallblake Intl-ORD Chicago O'Hare Intl
25h 03m2 stops Toronto Pearson Intl Ottawa
$1,736Multiple Airlines
Sun, Dec 27 - Sat, Jan 2

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American Airlines flights from Illinois to Anguilla

Our best American Airlines deals on Illinois to Anguilla flight tickets
American Airlines
Dec 8
ORD7:50 pmChicago O'Hare Intl
17h 07m
1 stop
AXA2:57 pmThe Valley Wallblake Intl
Dec 15
AXA3:37 pmThe Valley Wallblake Intl
11h 07m
1 stop
ORD12:44 amChicago O'Hare Intl
$712
American Airlines
Dec 8
ORD9:06 pmChicago O'Hare Intl
15h 51m
2 stops
AXA2:57 pmThe Valley Wallblake Intl
Dec 15
AXA5:45 pmThe Valley Wallblake Intl
15h 42m
2 stops
ORD7:27 amChicago O'Hare Intl
$717
American Airlines
Nov 1
ORD6:05 pmChicago O'Hare Intl
21h 00m
1 stop
AXA5:05 pmThe Valley Wallblake Intl
Nov 4
AXA5:45 pmThe Valley Wallblake Intl
17h 45m
1 stop
ORD9:30 amChicago O'Hare Intl
$728

United Airlines flights from Illinois to Anguilla

Our best United Airlines deals on Illinois to Anguilla flight tickets
United Airlines
Aug 21
ORD6:15 pmChicago O'Hare Intl
22h 20m
2 stops
AXA5:35 pmThe Valley Wallblake Intl
Aug 29
AXA9:46 amThe Valley Wallblake Intl
12h 21m
2 stops
ORD9:07 pmChicago O'Hare Intl
$2,082
United Airlines
Jan 26
ORD4:45 pmChicago O'Hare Intl
22h 50m
2 stops
AXA5:35 pmThe Valley Wallblake Intl
Jan 28
AXA9:46 amThe Valley Wallblake Intl
15h 56m
2 stops
ORD11:42 pmChicago O'Hare Intl
$2,972
United Airlines
Jan 26
ORD9:30 pmChicago O'Hare Intl
18h 05m
2 stops
AXA5:35 pmThe Valley Wallblake Intl
Jan 28
AXA9:46 amThe Valley Wallblake Intl
10h 59m
1 stop
ORD6:45 pmChicago O'Hare Intl
$3,015

momondo Fare Finder

 
Customize your flight search to find flights from Illinois to Anguilla that fit within your specific budget. Explore options based on user searches and filter the results based on your desired price range. Find flights that match your budget for a cost-effective journey. Over the last 7 days, momondo users made 832,500 searches. Data last updated August 15, 2026.
Use the filters below to find and compare flights from Illinois to Anguilla that are best for you.

Fly from

Fly to

Route

Depart

Return

Price

Cheapest round-trip
Quickest round-trip

ChicagoThe Valley

ORD Chicago O'Hare Intl - AXA The Valley Wallblake Intl

ORDAXA

Chicago O'Hare Intl

Tue 12/8

7:50 pm-2:57 pm

1 stop17h 07m

The Valley Wallblake Intl

Tue 12/15

3:37 pm-12:44 am

1 stop11h 07m

$712

ChicagoThe Valley

ORD Chicago O'Hare Intl - AXA The Valley Wallblake Intl

ORDAXA

Chicago O'Hare Intl

Tue 12/8

9:06 pm-2:57 pm

2 stops15h 51m

The Valley Wallblake Intl

Tue 12/15

5:45 pm-7:27 am

2 stops15h 42m

$717

ChicagoThe Valley

ORD Chicago O'Hare Intl - AXA The Valley Wallblake Intl

ORDAXA

Chicago O'Hare Intl

Tue 12/8

9:06 pm-2:57 pm

2 stops15h 51m

The Valley Wallblake Intl

Tue 12/15

3:37 pm-8:00 am

1 stop18h 23m

$717

ChicagoThe Valley

ORD Chicago O'Hare Intl - AXA The Valley Wallblake Intl

ORDAXA

Chicago O'Hare Intl

Tue 12/8

9:06 pm-2:57 pm

2 stops15h 51m

The Valley Wallblake Intl

Tue 12/15

5:45 pm-9:30 am

1 stop17h 45m

$717

ChicagoThe Valley

ORD Chicago O'Hare Intl - AXA The Valley Wallblake Intl

ORDAXA

Chicago O'Hare Intl

Sun 12/27

10:05 am-5:25 pm

2 stops29h 20m

The Valley Wallblake Intl

Sat 1/2

9:00 am-7:55 pm

1 stop12h 55m

$1,537

ChicagoThe Valley

ORD Chicago O'Hare Intl - AXA The Valley Wallblake Intl

ORDAXA

Chicago O'Hare Intl

Sun 12/27

3:45 pm-5:25 pm

3 stops23h 40m

The Valley Wallblake Intl

Sat 1/2

9:00 am-7:55 pm

1 stop12h 55m

$1,627

ChicagoThe Valley

ORD Chicago O'Hare Intl - AXA The Valley Wallblake Intl

ORDAXA

Chicago O'Hare Intl

Mon 8/31

8:55 am-5:35 pm

2 stops31h 40m

The Valley Wallblake Intl

Fri 9/4

9:46 am-8:05 pm

2 stops35h 19m

$1,634

ChicagoThe Valley

ORD Chicago O'Hare Intl - AXA The Valley Wallblake Intl

ORDAXA

Chicago O'Hare Intl

Wed 9/30

8:55 am-5:35 pm

2 stops31h 40m

The Valley Wallblake Intl

Sat 10/3

9:46 am-8:05 pm

2 stops11h 19m

$1,634

ChicagoThe Valley

ORD Chicago O'Hare Intl - AXA The Valley Wallblake Intl

ORDAXA

Chicago O'Hare Intl

Mon 8/31

8:55 am-5:35 pm

2 stops31h 40m

The Valley Wallblake Intl

Fri 9/4

9:46 am-8:05 pm

2 stops35h 19m

$1,634

ChicagoThe Valley

ORD Chicago O'Hare Intl - AXA The Valley Wallblake Intl

ORDAXA

Chicago O'Hare Intl

Sun 12/27

3:45 pm-5:25 pm

3 stops23h 40m

The Valley Wallblake Intl

Sat 1/2

9:00 am-8:03 am

2 stops25h 03m

$1,736

Flights are sorted by cheapest round-trip flights first.

Showing 1-10 of 16 resultsSorted by cheapest first
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See travel insights to Anguilla from

How to get the cheapest flight ticket from Illinois to Anguilla

Look no further. We've gone through all the searches for this route on momondo so you have the important information and insights to find the cheapest flight ticket for your trip

What is the cheapest airline that flies from Illinois to Anguilla?

American Airlines is the most popular carrier operating from Illinois to Anguilla

Cheap Illinois to Anguilla flight deals and tips

Find info about flight duration, direct flights, and airports for your flight from Illinois to Anguilla

Fastest flight time

7h 15m

Direct flights

None
The fastest flight from Illinois to Anguilla takes 7h 15m
There are no direct flights from Illinois to Anguilla. There are no popular flight routes from Illinois to Anguilla.
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Frequently asked questions about flying from Illinois to Anguilla

  • When did momondo last update prices for flights from Illinois to Anguilla?

    Prices for flights from Illinois to Anguilla refresh daily.

  • How many operators does momondo search for flights from Illinois to Anguilla?

  • How old do you have to be to fly from Illinois to Anguilla?

    Although the minimum age for a child to fly alone is five, airlines that offer an unaccompanied minor (UMNR) service may have their own age limits, which could be impacted by factors such as flight length, timing, and layovers. It is recommended that you verify with the airline you are booking with for travel from Illinois to Anguilla.

  • What documentation or ID do you need to fly to Anguilla?

    The required travel and health documents for your Anguilla trip may vary depending on your itinerary and personal circumstances. As a general rule, you should carry multiple documents, including a national ID card or driver's license and a passport valid for six months after your intended arrival at Anguilla. We recommend that you seek guidance from your airline or a reliable third party such as IATA.

Best airlines flying from Illinois to Anguilla

Compare and see reviews for airlines that fly from Illinois to Anguilla with momondo
Airline
Rating
Free Cancellation
Price
American AirlinesPriceFrom $529Free CancellationRating
7.1
11,941 reviews
Search American Airlines flights

Why use momondo?

Why should I use momondo to find a flight deal from Illinois to Anguilla?

It is quick and easy to find Illinois to Anguilla flights on momondo. We search and return numerous flight options from various airlines and agents. You can then use our filters to narrow your search until you have found the most convenient flight to Anguilla that suits you.

Can I find flights from Illinois to Anguilla with flexible booking policies on momondo?

All flight searches from Illinois to Anguilla on momondo can be filtered to show those which offer flexible booking policies.

How can momondo help me find flights from Illinois to Anguilla?

momondo provides multiple filters to help you find the best flight to Anguilla from Illinois. Filter by price, airline, airports, cabin, aircraft, payment method, number of stops and more.

I’m not ready to book a flight from Illinois to Anguilla right now. Can momondo alert me if prices change?

Price alerts on flights to Anguilla from Illinois are quick and easy to set up on momondo. Simply perform a search and select the price alert feature. It is as simple as that.

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Popular cities in Anguilla

Popular flights according to clicks in the last 7 days on momondo
Flights to The Valleyfrom $620